Round Hill Hotel & Villas

Once part of a 19th century 100-acre sugar plantation owned by an English Lord, the island paradise of Round Hill Hotel and Villas now sits on its own 110-acre peninsula in dazzling Montego Bay. Ralph Lauren personally designed all 36 ocean-front guest rooms of the famed Pineapple House. Plush, laid-back, but sophisticated comfort alongside the wonderful amenities brought into this colonial structure, are the highlights of Ralph Lauren’s masterly talent for stately decor and room design.

For those who are looking for more privacy, Round Hill also offers 27 individual private villas ranging from two to six bedrooms, each nestled in the hillside overlooking the sea, where guests can book either as a complete villa with private pool and delicious flower-filled gardens, with a dedicated staff, or as individual villa suites, all unique in design and style.

An entire 18th century estate adjacent to the hotel was turned into one of the world’s most exclusive full service spas with a beautiful pool on the front lawn overlooking the ocean. A new state of the air conditioned art fitness center and open air yoga pavilion boasts beautiful sweeping seaside views.

With a full array of water sports, tennis, the complimentary Pineapple kids club, and nearby golf, shopping in Montego Bay, wedding and event services, succulent farm-to-table fresh cuisine, featuring the James Beard award-winner, Chef Martin Maginley, the diverse range of nightly entertainment… it is a wonder that Round Hill is known for its simplicity and calm, its subdued and sublime aristocratic atmosphere. It was no secret that Round Hill was the favored destination of Noel Coward, Adele Astaire, Cole Porter, Grace Kelly, Bill and Babe Paley, Lord and Lady Ednam, Mr. and Mrs. Oscar Hammerstein, Viscount and Viscountess Rothermere, Errol Flynn, Clarke Gable, Rosalind Russell, and JFK and Jackie.

Of course, it doesn’t hurt to have a round-the-clock and delightful staff of 220 at your fingertips. The Jamaican nannies at Round Hill are considered treasures, beloved by both the kids and their parents.

Both the resort and its spa services have received numerous prestigious awards throughout its history – with the more recent 2015 Trip Advisor Hall of Fame Certificate of Excellence and the World Travel Awards 2014 World’s Leading Villa Resort for eleven consecutive years!